Metal–ligand multiple bonds as frustrated Lewis pairs for C–H functionalization

• Matthew T. Whited

Beilstein J. Org. Chem. 2012, 8, 1554–1563, doi:10.3762/bjoc.8.177

• of isocyanates to ruthenium(II) silylenes [58] (Scheme 8). These complexes do not react with nonpolar substrates (although a possible cycloaddition with azobenzene was reported), and the overall cycloaddition was found to proceed through initial nucleophilic attack at an electrophilic silylene

• were observed when carbon dioxide, carbonyl sulfide, and isocyanates were utilized, cleanly generating the Ir(I) carbonyl as a byproduct (Scheme 11) [71]. The nucleophilicity of the iridium center was demonstrated through a series of experiments. First, it was noted that the carbene complex does not

Derivatives of phenyl tribromomethyl sulfone as novel compounds with potential pesticidal activity

• Krzysztof M. Borys,
• Maciej D. Korzyński and
• Zbigniew Ochal

Beilstein J. Org. Chem. 2012, 8, 259–265, doi:10.3762/bjoc.8.27

• with carbon disulfide (Scheme 8) [17]. Moreover, 11h was subjected to the reaction with aromatic isocyanates to give benzimidazolthiocarbamates 11i and 11j. The synthesized compounds were tested for their fungicidal activity. The evaluation was carried out by determining the percentage inhibition of

Amines as key building blocks in Pd-assisted multicomponent processes

• Didier Bouyssi,
• Nuno Monteiro and
• Geneviève Balme

Beilstein J. Org. Chem. 2011, 7, 1387–1406, doi:10.3762/bjoc.7.163

• -allenylamines, organic halides and isocyanates [42]. In this process, there is first a carbopalladation of the functionalized allene with the aryl iodide, followed by reaction of the internal aza-nucleophile with the highly electrophilic isocyanate derivative, before premature trapping of the initially formed π

• derivatives through a one-pot palladium-catalyzed double C–N arylation in combination with a S-arylation. Synthesis of substituted imidazolidinones through a palladium-catalyzed three-component reaction of 2,3-allenyl amines, organic halides and isocyanates. Synthesis of 2,3-diarylated amines through a

(Pseudo)amide-linked oligosaccharide mimetics: molecular recognition and supramolecular properties

• José L. Jiménez Blanco,
• Fernando Ortega-Caballero,
• Carmen Ortiz Mellet and
• José M. García Fernández

Beilstein J. Org. Chem. 2010, 6, No. 20, doi:10.3762/bjoc.6.20

• followed by treatment with yellow mercury (II) oxide [68]. There are two general strategies to access pseudoamide-type oligosaccharide mimics: i) nucleophilic addition of sugar derivatives to carbohydrate isocyanates, isothiocyanates or isocyanides; and ii) conversion of sugar azides into glycosyl

• or sugars, respectively, and glycosyl-isocyanates [73][74] or isocyanides [75]. However, the experimental difficulties in handling isocyanates has led to the preferential use of sugar carbodiimides as key intermediates for the preparation of glycosylureido sugars [76][77][78][79]. From the large

Controlling hazardous chemicals in microreactors: Synthesis with iodine azide

• Johan C. Brandt and
• Thomas Wirth

Beilstein J. Org. Chem. 2009, 5, No. 30, doi:10.3762/bjoc.5.30

• Discussion The radical addition of azide to aldehydes 1 initially forms acyl azides 2 which directly rearrange in a Curtius rearrangement to the corresponding isocyanates 3. Isocyanates are very reactive themselves and offer a wide range of possible conversions. An excess of azide leads to the formation of

• ratio of about 1:3 of trimethylsilyl azide and trimethylsilyl chloride upon reaction with iodine monochloride. This mixture was not efficient in the reaction with aldehydes, only an unidentifiable mixture of products was obtained. The reactivity of carbamoyl azides is analogous to isocyanates, compound

A facile synthesis and fungicidal activities of 2-(alkylamino)-5,6-dimethylthieno[2,3-d]pyrimidin- 4(3H)-ones

• Yang-Gen Hu,
• Ai-Hua Zheng,
• Xu-Zhi Ruan and
• Ming-Wu Ding

Beilstein J. Org. Chem. 2008, 4, No. 49, doi:10.3762/bjoc.4.49

• Education, Central China Normal University, Wuhan 430079, China 10.3762/bjoc.4.49 Abstract The aza-Wittig reactions of iminophosphorane 3 with aromatic isocyanates generated carbodiimides 4, which were reacted with alkylamines under mild conditions to give a series of 2-(alkylamino)-5,6-dimethylthieno[2,3

• activities against six kinds of fungi. Keywords: 2-(alkylamino)-5,6-dimethylthieno[2,3-d]pyrimidin-4(3H)-one; aza-Wittig reaction; fungicidal activity; synthesis; Introduction Over the past ten years, aza-Wittig reactions of functionalized iminophosphoranes with isocyanates have been applied to produce

• interested in the synthesis of a series of new heterocyclic compounds via aza-Wittig reaction of α- or β-(ethoxycarbonyl)-substituted iminophosphoranes with aromatic isocyanates and subsequent reaction with various nucleophiles under mild conditions [11][12][13][14]. Herein we wish to report an efficient